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Acetic Acid → HCID 25023595, 화합물

HRID 2076359
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HRID 2076359 반응식
[CH2:1]([N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][C:13]3[C:19](=O)[C:18]([CH2:26][CH2:27][F:28])([CH2:21][CH2:22][C:23](=[O:25])[CH3:24])[CH2:17][C:14]=32)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1CCCC1.C(O)(=O)C>C1(C)C=CC=CC=1.CCCCCCC.ClCCl>[CH2:1]([N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][C:13]3[C:19]4[C:18]([CH2:26][CH2:27][F:28])([CH2:21][CH2:22][C:23](=[O:25])[CH:24]=4)[CH2:17][C:14]=32)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 176Acetic AcidHCID 31268PyrrolidineHCID 59397215HCID 59397215, 화합물

생성물 1

HCID 25023595HCID 25023595, 화합물

시약·촉매·용매 2

HCID 1140Toluene용매HCID 21907733Dichloromethane heptane용매

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온도
90 °C

실험 절차

To a solution of 2-benzyl-7-(2-fluoroethyl)-7-(3-oxobutyl)-7,8-dihydrocyclopenta[e]indazol-6(2H)-one (10.8 g, 28.6 mmol) in 300 mL of toluene were added pyrrolidine (2.4 mL, 28.6 mmol) and acetic acid (1.64 mL, 28.6 mmol) and the solution was heated at 90° C. under nitrogen. After 15 hours, the solution was cooled to room temperature and partitioned between EtOAc and water. The organic phase was washed with 5% aqueous NaHCO3 and brine and dried over MgSO4. Evaporation of the solvent under vacuum gave a brown oil which was purified by chromatography on silica gel (1:2 to 1:1 EtOAc/hexanes) to give a sticky orange solid. The solid was dissolved in heptane-dichloromethane and then most of the dichloromethane was evaporated under reduced pressure. The resulting precipitated solid was isolated by filtration to give 2-benzyl-9a-(2-fluoroethyl)-8,9,9a,10-tetrahydroindeno[2,1-e]indazol-7(2H) -one.

후처리

  1. temperaturethe solution was cooled to room temperature
  2. custompartitioned between EtOAc and water
  3. washThe organic phase was washed with 5% aqueous NaHCO3 and brine
  4. dry with materialdried over MgSO4
  5. customEvaporation of the solvent under vacuum
  6. customgave a brown oil which
  7. customwas purified by chromatography on silica gel (1:2 to 1:1 EtOAc/hexanes)
  8. customto give a sticky orange solid
  9. custommost of the dichloromethane was evaporated under reduced pressure
  10. customThe resulting precipitated solid
  11. customwas isolated by filtration

출처 및 근거

ORD 기록
ord-a76086e7fe90420a856cff39c463235a
출처 데이터셋
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07923568B2

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